Pennywise vs. Randall Flagg: Which Is Stephen King's Greatest Villain?
In the race to be Stephen King's greatest villain, two major contenders emerge, IT's Pennywise the Clown and The Stand's Randall Flagg. There's certainly no shortage of terrifying monsters, of both the humanoid and non-humanoid varieties, living within King's sprawling multiverse. Still, Pennywise and Flagg consistently rise above the rest when it comes to recognition, which is certainly at least partially attributable to them serving as the big bads in IT and The Stand, arguably King's two greatest works aside from The Dark Tower series.
Even without considering the books in which Pennywise and Randall Flagg reside, though, both characters are extremely memorable and are likely to live in the minds of those who read IT and The Stand long after they've finished the last page. Neither villain has been limited to only one of King's stories, either, seemingly always lurking somewhere in the background of King's world, ready to influence something or someone. The origins of both beings are also fairly mysterious, with not much revealed about either villain's true birth.
If there's one thing that's not in question, it's that Pennywise and Randall Flagg are both entities that no one would ever really want to encounter. Select forces of good, such as The Stand's Mother Abigail, in King's multiverse may prove able to weaken or defeat them, at least temporarily, but the vast majority of those who ever come face to face with Pennywise or Flagg are left murdered, maimed, or both. Still, there can only be one monster declared to be Stephen King's greatest villain, and here's who takes the crown.
When it comes to being a villain in a Stephen King story, IT's Pennywise and The Stand's Randall Flagg do have some similarities, beyond their inherent love for power and cruelty. One similar power they have is the ability to shapeshift, which has been seen in the TV and movie adaptations of IT and The Stand, but is much more pronounced in King's books. On a basic, more primal level though, Pennywise the clown is just downright scarier than Flagg. It's a monstrous clown with enormous sharp teeth, after all, and most of the time, Flagg just appears to be some guy in cowboy boots and a denim vest. Pennywise's ability to change itself into other forms - its true form, of course, being a kind of interdimensional spider - also seems much less limited than Flagg's.
Pennywise's ability to control and influence the minds of humans, also seems to be much harder to overcome than Flagg's mental powers. Flagg can mentally project himself across distances, and make others see scary things, but he can't outright mentally dominate people like Pennywise does via its Deadlights. Pennywise is also more dangerous in general, as, while Flagg needs the adulation of followers to fully employ his powers, Pennywise lives simply to eat. One could theoretically survive Flagg by appealing to his vanity, and ultimately pledging to serve him. Pennywise only keeps humans alive long enough to salt the meat with their fear, or use them to accomplish a specific task, like Henry Bowers.
While IT's Pennywise certainly has a lot going in its favor as far as being Stephen King's greatest villain, The Stand's Randall Flagg has many positives, too. For one, he's not quite as susceptible to the power of belief as Pennywise is. While Flagg does draw on the worship of his unholy Las Vegas congregation to be able to pull off his greatest feats of evil, losing some of that worship doesn't make him a pushover. As seen in both IT movies and to a lesser extent the book, when the fear that Pennywise draws on is taken away, what's left behind is a much less formidable monster, making him able to be defeated by The Losers' Club.
For Randall Flagg to be beaten in The Stand, the literal hand of God has to show up and lightning blast the demonic leader to kingdom come. Even then, as the unabridged ending of The Stand novel and the 2020 miniseries, Flagg may have been defeated, but he wasn't killed. In fact, many of King's constant readers wonder if the multi-aliased Randall Flagg can ever truly die. Some also wonder this about Pennywise, but its ability to survive anything is much more in question. Flagg, as shown in some of his other King book appearances, can also literally raise the dead, something it's never been shown Pennywise can do. There's also something to be said for the effectiveness of a villain that comes in the guise of a friend and seeks to corrupt humanity instead of just killing people. Killing people is one thing, but making them kill each other is another gift entirely.
As documented above, IT's Pennywise and The Stand's Randall Flagg both have points in their favor in the battle to be named Stephen King's greatest villain. In the end, though, the distinction goes to Flagg because of two specific things. One, Stephen King himself believes Randall Flagg to be his best bad guy, and the word of the master of horror has to count for something. Additionally, though, Flagg is King's greater scope villain, and could be considered the biggest evil presence in the entire King multiverse. This is driven home by Flagg's role in the sprawling Dark Tower franchise, where he's seemingly always plotting to gain more power.
For as menacing and bone-chilling a Stephen King villain as Pennywise is, he basically limits his carnage to Derry, Maine. Flagg turns up just about everywhere, always ready to prey on humanity's weaknesses to serve his own ends, and as seen in The Stand, capitalize on the very apocalypse as a chance to ascend to the throne he feels he deserves. Pennywise probably won't bother someone who never visits IT's cursed town of Derry, but Flagg is so malevolent he feels like someone who might try to actually employ Pennywise's services, unleashing the clown worldwide if possible. Pennywise may embody the emotion of fear, but Randall Flagg embodies the very concept of evil, ever-watching, ever-plotting, and always ready to make things worse. He's a cancer, and one whose influence spreads nearly as quickly as Captain Trips itself.